Tag: M.W=100-200

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H3F3N2

Synthesis of 3-methoxy-5-nitro-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)pyridine To a stirred solution of 2-chloro-3-methoxy-5-nitropyridine (2 g, 10.60 mmol) in DMSO (30 mL) under an argon atmosphere were added potassium carbonate (6.70 g, 48.61 mmol) and 4-(trifluoromethyl)-1H-imidazole (1.7 g, 12.76 mmol) at room temperature. The reaction mixture was stirred at 50 C. for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to afford 3-methoxy-5-nitro-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)pyridine (1.4 g, 46%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.65 (s, 1H), 8.45 (s, 1H), 8.44 (s, 1H), 4.11 (s, 3H); LCMS: 288.8 (M+1); (column; X-Select CSH C-18 (50*3.0 mm, 3.5 mum); RT 3.46 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/CH2Cl2 (Rf: 0.4).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
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Imidazole | C3H4N2 – PubChem

Reference of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 1 -methyl- lH-imidazole-4-carbaldehyde (lg, 9.1 mmol, 1.1 eq.) in THF (12 mL) is added P(Bu)3 (2.16 mL, 8.7 mmol, 1.05 eq.) and the reaction mixture is heated at 50C for 5 min. teri-butyl ester acrylate (1.2 mL, 8.3 mmol, 1 eq.) is added and the reaction mixture is stirred at 80C for 3h. teri-butyl ester acrylate (0.3 mL, 0.25 eq.) is added and this process (heating 3h and addition of tert- butyl ester acrylate) is repeated until no evolution is observed by TLC (EtOAc) and UPLC/MS. The reaction mixture is concentrated in vacuo and the residue is purified by flash chromatography on silica gel (eluting with Heptane/EtOAc 100/0 to 0/100) to afford the expected product. LCMS: MW (calcd): 238; m/z MW (obsd): 239 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; BREBION, Franck, Laurent; ALVEY, Luke, Jonathan; AMANTINI, David; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene, Marie; PEIXOTO, Christophe; VARIN, Marie, Laurence, Claire; DE CEUNINCK, Frederic, Andre; POP-BOTEZ, Iuliana, Ecaterina; (317 pag.)WO2016/102347; (2016); A1;,
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Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The ethyl 1-(4-cyanomethyl-1-oxoindan-2yl)imidazole-2-carboxylate can be obtained in the following manner: a solution of 1.8 g of ethyl imidazole-2-carboxylate in 30 ml of acetone is supplemented with 8.6 g of potassium carbonate. This suspension is heated at reflux for 15 minutes and then a solution of 3.22 g of 2-bromo-4-(cyanomethyl)indan-1-one in 30 ml of acetone is added. After stirring for 4 hours at reflux temperature, the reaction medium is brought to a temperature close to 20° C. and filtered on sintered glass. The filtrate is evaporated and 2.7 g of a black solid are obtained. The purification by flash chromatography on a silica column (eluent: dichloromethane-ethyl acetate (50-50 by volume)) of this solid gives 0.62 g of ethyl 1-(4-cyanomethyl-1-oxoindan-2-yl)imidazole-2-carboxylate in the form of a brown solid [mass spectrum m/z 309 (M+), 236 ((M-CO2 Et), +), 141 ((C6 H9 N2)+), 68((C3 H4)+)].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-imidazole-2-carboxylate, its application will become more common.

Reference:
Patent; Rhone Poulenc Rorer S.A.; US5990108; (1999); A;,
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Imidazole | C3H4N2 – PubChem

Related Products of 496-46-8, These common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A steel autoclave (25 cm3) was charged with 2, 3 or 5 (2.5 mmol), filled with liquid CO2 to a pressure of 60 barand cooled to 5 C. Then nitrating agent (5.5-10.0 mmol, see Table 1)dissolved in liquid CO2 (~3.5 g) was added in ten steps for 15 min. Thereaction mixture was gradually warmed to room temperature and stirredfor 2 h at 80 bar [for supercritical conditions (Table 1, entry 8), the temperatureand the pressure were raised to 45 C and 100 bar, respectively,after the addition of the nitrating agent]. After 2 h stirring, the ice water(2 ml) was pressurized into the autoclave to destroy the access of nitratingagent. The CO2 was removed and additional amount of ice water (20 ml)was added to the residue at atmospheric pressure. The precipitate wasfiltered and dried at 40 C for 2 h to afford nitration product 1, 4 or 6, respectively. Isolated yields are given in Table 1. The NMR spectra ofknown compounds 1a,2 1b14 and 615 correspond to reported data. Meltingpoints of compounds 1a-c and 4 were not observed. Temperatures TID atwhich originally colorless solids started to become dark (initiation of adecomposition) are given below.1,4-Dinitroglycoluril 1a: TID 192 C. 1H NMR, d: 6.03 (s, 2 H, CH),9.83 (s, 2 H, NH). 13C NMR, d: 149.0, 63.8. 14N NMR, d: -39.5.3a,6a-Dimethyl-1,4-dinitrotetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione 1b: TID 194 C. 1H NMR, d: 1.82 (s, 6 H, Me), 9.94 (s, 2 H, NH).13C NMR, d: 146.5, 76.9, 17.8. 14N NMR, d: -46.6.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zharkov, Mikhail N.; Kuchurov, Ilya V.; Fomenkov, Igor V.; Zlotin, Sergei G.; Tartakovsky, Vladimir A.; Mendeleev Communications; vol. 25; 1; (2015); p. 15 – 16;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4887-88-1, These common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step C – Methyl 5-{5-bromo-1 A£benztmidazoi-1-yl)-3-{[f°/£ butyl{dimethyi)si.yl]oxy}thlophene-2-carboxyiate and methyl 5-(6-bromo1 H- be?zimldazo.-1-yl)-3″{[/erf”btyf(dimethyi)silyl]oxy}thiophene-2-carboxy.ate {title compounds)To a solution of crude, impure 5-bromobe?zimidazo.e (48.2 g) and methyl 2- chioro-3-oxo-2,3-dihydrothiophene-2-carboxylate (42 g, 220 mmol) In 800 mL of CHCl3 was added Mmethyiimidazote (28 rrsL, 350 mmol). After 16 h, N- roethyl imidazole (17 mL, 220 mmol) and (38 g, 240 mmoi) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto ceiite. The crude mixture was purified by flash column chromatography (Q- 25% EtOAc:hexa?es) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 4 eluiing first and 29.2 g of Intermediate 5 elupsilonti?g second (58%), (Intermediate 4, 5~thetar) 1H NMR (400 MHz, drthetayUSDG) delta 8.77 (s, 1H)1 8.01 (d J – 1.6 Hz, IH), 7.76 (d, J -8.8 Hz1 IH)1 7.56{dd, J ^8.8 and 1.6 Hz5 1 H)1 7.25 (s, 1 H), 3.76 (s, 3H)1 0.99 {s, 9H), 0.27 (ss 6H). (trfermediate 5, 6- Br) 1H NyR (400 MHz1 (J6-DMSO) delta 8.71 (S1 1H), 7.88 (d, ./ – 1 ,6 Hz, 1H), 7,73 (d, J ^ 8.8 Hz5 I H), 7.50 (, ./=8.8 and 2.0 Hz1 I H)1 7.28 (s, 1H)1 3.77 (s, 3H), 0.99 (s, 9H), 0.26 (s, 6H).

Statistics shows that 5-Bromo-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 4887-88-1.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/143456; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 36947-68-9, These common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example A29 A mixture of 2-isopropylimidazole (3.0 g, 27.2 mmol) and DIEA (5.28 g, 40.9 mmol) in DCM (75 mL) was treated drop-wise with methoxyethoxymethyl chloride [MEM-Cl](4.24 g, 34.0 mmol) and stirred at RT for 16 h. The mixture was washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford 2-isopropyl-1-((2-methoxyethoxy)methyl)-1H-imidazole (3.91 g, 72%). 1H NMR (400 MHz, DMSO-d6): delta 7.11 (d, J=1.3 Hz, 1H), 6.74 (d, J=1.3 Hz, 1H), 5.30 (s, 2H), 3.47-3.46 (m, 2H), 3.38-3.37 (m, 2H), 3.19 (s, 3H), 3.08-3.07 (m, 1H), 1.18 (d, J=6.8 Hz, 6H).

Statistics shows that 2-Isopropyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 36947-68-9.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1072-84-0, name is 1H-Imidazole-4-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 1H-Imidazole-4-carboxylic acid

Example 85 To a solution of 200 mg of 4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidine monohydrochloride in 5 ml of dimethylformamide, 111 mul of triethylamine, 107 mg of imidazole-4-carboxylic acid, 161 mg of 1-hydroxybenzotriazole and 228 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added at ambient temperature. After stirring at ambient temperature overnight, the reaction mixture was concentrated under reduced pressure. After 50 ml of chloroform and 15 ml of saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, the organic layer was fractionated and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol-ammonia water) to give 280 mg of colorless oil. The oil obtained was dissolved in 2 ml of ethanol, and 226 mul of 4N hydrochloric acid-ethyl acetate was added to the solution. The precipitated crystals were collected by filtration and washed with diethyl ether. The crystals were recrystallized from ethanol-diethyl ether to give 191 mg of 4-[(E)-2-(2,6-dimethylphenyl)vinyl]-1-(1H-imidazol-4-ylcarbonyl)piperidine monohydrochloride.

The synthetic route of 1H-Imidazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; Kotobuki Pharmaceutical Co., Ltd.; EP1602645; (2005); A1;,
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Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, These common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Scheme 1Intermediate A1 : 2-Chloro-1-(tetrahvdropyran-2-yl)-1 H-benzimidazoleA 10 I reactor is charged under argon and with stirring with 2.5 I of THF, 180 g of 2- chlorobenzimidazole (1.18 mol) and 325 ml of 3,4-dihydro-2H-pyran (6.56 mol, 3 eq.). The reactor is heated until dissolution takes place (temperature of the medium: 40C). Then 6.3 g of para-toluenesulphonic acid (0.033 mol, 0.028 eq.) are introduced. The temperature is maintained at between 49 and 52C for 2.5 hours. The system is cooled to 12C and 7.65 g of sodium methoxide (0.142 mol, 0.12 eq.) are added, with stirring maintained, over a total time of 15 minutes. The temperature is then brought to 18C, 5 I of n-heptane are added, and the whole is filtered over 300 g of Clarcel FLO-M, the retentate being washed with 5 I of n- heptane. The filtrate is concentrated to dryness under reduced pressure to give 292.6 g of 2- chloro-1-(tetrahydropyran-2-yl)-1 H-benzimidazole in the form of a slightly yellow oil (quantitative yield). 1H NMR (400 MHz, DMSO-d6): 1.42 to 2.01 (m, 5H); 2.21 to 2.34 (m, 1 H); 3.69 to 3.78 (m, 1 H); 4.12 (d, J=1 1.4 Hz, 1 H); 5.72 (dd, J=2.4 and 1 1.2 Hz, 1 H); 7.22 to 7.34 (m, 2H); 7.62 (d, J=7.2 Hz, 1 H); 7.78 (d, J=7.2 Hz, 1 H).

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; AROKIASSAMY, Nathalie; BILLOT, Pascal; CARRY, Jean-Christophe; CLAVIERES, Patrick; CLERC, Francois; CROCQ – STUERGA, Veronique; LACHAUD, Sylvette; LIENARD, Philippe; MENEGOTTO, Jerome; SCHIO, Laurent; WO2012/66486; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2302-25-2 as follows. name: 4-Bromo-1H-imidazole

In nitrogen atmosphere to 5.0g (34mmol) 4-bromo-1H-imidazole, 7.14g (35mmol) Iodobenzene, 0.27g (4.25mmol) copper, 3.5g (25.3mmol) drying solvent xylene potassium carbonate in the reflux time 3 180 C senses a rotation velocity of the disk. 100 ml toluene cooled and room temperature after reaction adding woman star and aspiration filtered out, after silica gel column, then concentrated, acetic acid ethyl/methanol mixed solvent film by cleaning the solid compound (4.0g) of 53% are obtained.

According to the analysis of related databases, 2302-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Choe, Don Soo; Jo, Yun Hwan; (92 pag.)KR2015/80966; (2015); A;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 2-(1H-Imidazol-1-yl)acetonitrile

A 25 mL flask is charged with powdered KOH (239 mg, 4.26 mmol), DMSO (5 mL), purged with Argon and is cooled at 10C with a water bath. A solution of 2-imidazol-1-ylacetonitrile (228 mg, 2.13 mmol) and CS2 (257 mu, 4.26 mmol) in DMSO (2 mL) is then added slowly to give an orange mixture. The cooling bath is removed and the reaction is stirred at room temperature for 15 minutes. A solution of [2-chloro-1-[2-chloro-4-[(6-methoxy-3-pyridyl)oxy]phenyl]ethyl] methanesulfonate (620 mg, 1.59 mmol) in DMSO (2 mL) is then added dropwise. After 4 hours, the reaction mixture is poured into H20 (15 mL). The aqueous phase is extracted with dichloromethane, the combined organic phases are washed with brine, dried with Na2S04, filtered and are evaporated to give a crude pale yellow residue. Purification by chromatography on silica gel (heptanes / EtOAc, 1 :1?1 :3?1 :4) afford (2E)-2- [4-[2-chloro-4-[(6-methoxy-3-pyridyl)oxy]phenyl]-1 ,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile (compound l.bj.25) as a white foam. Mp = 88-91 C. H-NMR (400 MHz, CDCI3): delta = 7.96 (d, J = 3.0 Hz, 1 H), 7.63 (s, 1 H), 7.50 (d, J = 8.9 Hz, 1 H), 7.31 (dd, J = 3.0, 8.9 Hz, 1 H), 7.16 (s, 1 H), 7.05 (t, J = 1.3 Hz, 1 H), 6.97 (d, J = 2.7 Hz, 1 H), 6.88 (dd, J = 2.7, 8.5 Hz, 1 H), 6.79 (d, J = 8.5 Hz, 1 H), 5.65 (dd, J = 5.1 , 8.3 Hz, 1 H), 3.95 (s, 3H), 3.92 (dd, J = 5.1 , 12.0 Hz, 1 H), 3.74 (dd, J = 8.3, 12.0 Hz, 1 H). MS (ESI): m/z = 443, 445 (M+1 ).

The synthetic route of 2-(1H-Imidazol-1-yl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien Daniel Henri; MAITY, Pulakesh; RAJAN, Ramya; JEANMART, Stephane Andre Marie; LAMBERTH, Clemens; WO2015/162271; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem